(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chloride → HCID 59164388, compound

HRID 1441487Notes

Reaction equation

HRID 1441487 reaction equation
Cl.[CH:2]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][N:20]=3)[CH2:17][NH:16][CH2:15][CH2:14]4)=[CH:7][CH:6]=2)[CH2:4][CH2:3]1.[CH3:21][C@@:22]1([CH2:29][S:30](Cl)(=[O:32])=[O:31])[C:26](=[O:27])[NH:25][C:24](=[O:28])[NH:23]1>CCOC(C)=O.CCOC(C)=O.CO>[CH:2]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][N:20]=3)[CH2:17][N:16]([S:30]([CH2:29][C@@:22]3([CH3:21])[NH:23][C:24](=[O:28])[NH:25][C:26]3=[O:27])(=[O:31])=[O:32])[CH2:15][CH2:14]4)=[CH:7][CH:6]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 66734846HCID 66734846, compound

Product 1

HCID 59164388HCID 59164388, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

The title compound was prepared from 6-(6-cyclopropylpyridin-3-yl)-1,2,3,4-tetrahydro-2,7-naphthyridine hydrochloride (0.63 mmol) and [(4S)-4-methyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride (0.70 mmol) following the general procedure of Example 1. Column chromatography with neat EtOAc and EtOAc-MeOH (9:1) as eluents gave 0.060 g of almost pure product. Recrystallisation from 99% EtOH gave 0.019 g (7.0%) of the title compound as white solid.

Workup

  1. customRecrystallisation from 99% EtOH

Sources & evidence

ORD record
ord-cdb4e42fca5047df8ca259baca5a915e
Source dataset
uspto-grants-2010_02
Patent number
US07655664B2

Reaction notes

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